EP0464448A1 - Colorants réactifs azoiques ayant au moins deux ancres halogénotriazine - Google Patents
Colorants réactifs azoiques ayant au moins deux ancres halogénotriazine Download PDFInfo
- Publication number
- EP0464448A1 EP0464448A1 EP91109927A EP91109927A EP0464448A1 EP 0464448 A1 EP0464448 A1 EP 0464448A1 EP 91109927 A EP91109927 A EP 91109927A EP 91109927 A EP91109927 A EP 91109927A EP 0464448 A1 EP0464448 A1 EP 0464448A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- hydroxysulfonyl
- dyes
- chlorine
- fluorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000987 azo dye Substances 0.000 title abstract 2
- -1 hydroxysulphonyl Chemical group 0.000 claims abstract description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 238000004043 dyeing Methods 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000985 reactive dye Substances 0.000 claims description 19
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 34
- 239000002253 acid Substances 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 description 16
- 238000010168 coupling process Methods 0.000 description 16
- 238000005859 coupling reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 2
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 2
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 2
- YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 2
- SEKQCTQOFVHEMA-UHFFFAOYSA-N 4-[[4-(3-amino-4-sulfoanilino)-6-chloro-1,3,5-triazin-2-yl]amino]benzene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(NC=2N=C(NC=3C(=CC(=CC=3)S(O)(=O)=O)S(O)(=O)=O)N=C(Cl)N=2)=C1 SEKQCTQOFVHEMA-UHFFFAOYSA-N 0.000 description 2
- 0 C*(C)(C)*(C=CC=C1)C=C1N(*)c1nc(Cl)nc(N/C(/C=C2)=C/C/*(/S(O)(=O)=O)=C\C2N=N[C@](C2O)C(S(O)(=O)=O)=CC(C3)=C2C(NC)=CC=*3S(O)(=O)=O)n1 Chemical compound C*(C)(C)*(C=CC=C1)C=C1N(*)c1nc(Cl)nc(N/C(/C=C2)=C/C/*(/S(O)(=O)=O)=C\C2N=N[C@](C2O)C(S(O)(=O)=O)=CC(C3)=C2C(NC)=CC=*3S(O)(=O)=O)n1 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 1
- WXUAZZARGUDIHU-UHFFFAOYSA-N 2-(ethylamino)-5-sulfobenzoic acid Chemical compound CCNC1=CC=C(S(O)(=O)=O)C=C1C(O)=O WXUAZZARGUDIHU-UHFFFAOYSA-N 0.000 description 1
- FOCNLZUSVWLFLK-UHFFFAOYSA-N 2-(ethylamino)benzene-1,4-disulfonic acid Chemical compound CCNC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O FOCNLZUSVWLFLK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FTIFXWCPLYLZAW-UHFFFAOYSA-N 2-[[4-(4-amino-3-sulfoanilino)-6-chloro-1,3,5-triazin-2-yl]amino]benzene-1,4-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1NC1=NC(Cl)=NC(NC=2C(=CC=C(C=2)S(O)(=O)=O)S(O)(=O)=O)=N1 FTIFXWCPLYLZAW-UHFFFAOYSA-N 0.000 description 1
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- POARFFINDDZLEI-UHFFFAOYSA-N 2-amino-5-chlorobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(Cl)C=C1S(O)(=O)=O POARFFINDDZLEI-UHFFFAOYSA-N 0.000 description 1
- YYRVBCBZQPTVEO-UHFFFAOYSA-N 2-amino-5-methylbenzene-1,4-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O YYRVBCBZQPTVEO-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- KQFHWXWVXYYVKU-UHFFFAOYSA-N 4-(ethylamino)benzene-1,3-disulfonic acid Chemical compound CCNC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O KQFHWXWVXYYVKU-UHFFFAOYSA-N 0.000 description 1
- KTXPEELQCZMXSR-UHFFFAOYSA-N 4-amino-6-chlorobenzene-1,3-disulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1S(O)(=O)=O KTXPEELQCZMXSR-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- QUFFRITXLMVPMV-UHFFFAOYSA-N 4-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 QUFFRITXLMVPMV-UHFFFAOYSA-N 0.000 description 1
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- JQLKQZOPUGCTLT-XAHDOWKMSA-N CNC(C(C(C1/N=N/C(CC(Nc2nc(NC(CCC(S(O)(=O)=O)=C3)C3S(O)(=O)=O)nc(Cl)n2)=CC2)C2S(O)(=O)=O)O)=C2CC1S(O)(=O)=O)=CCC2S(O)(=O)=O Chemical compound CNC(C(C(C1/N=N/C(CC(Nc2nc(NC(CCC(S(O)(=O)=O)=C3)C3S(O)(=O)=O)nc(Cl)n2)=CC2)C2S(O)(=O)=O)O)=C2CC1S(O)(=O)=O)=CCC2S(O)(=O)=O JQLKQZOPUGCTLT-XAHDOWKMSA-N 0.000 description 1
- ZCVVQJDENIXULX-QGOAFFKASA-N Cc1nc(Nc(cc2/N=N/C)ccc2S(O)(=O)=O)nc(C)n1 Chemical compound Cc1nc(Nc(cc2/N=N/C)ccc2S(O)(=O)=O)nc(C)n1 ZCVVQJDENIXULX-QGOAFFKASA-N 0.000 description 1
- LWYTVWIUDHZBHR-UHFFFAOYSA-N ClNC1=CC=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O Chemical compound ClNC1=CC=C(C(=C1)S(=O)(=O)O)S(=O)(=O)O LWYTVWIUDHZBHR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
Definitions
- the new azo reactive dyes of the formula I are given in the form of the free acids. However, their salts, in particular their alkali metal salts, are of course also included.
- JP-A-69 163/1985 describes reactive dyes which differ from those of the formula I in that the ring A there has neither a hydroxysulfonyl nor a carboxyl group, but rather an additional anchor based on the vinylsulfonyl radical.
- the older EP-A-387 589 relates to similar azo reactive dyes. However, they differ in the number of hydroxysulfonyl groups.
- the new dyes should also be able to be applied both cold and hot.
- R1 and R2 are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 2-methoxyethyl, 2- or 3-methoxypropyl, 2- or 4- Methoxybutyl, 2-ethoxyethyl, 2- or 3-ethoxypropyl, 2- or 4-ethoxybutyl, 2-chloroethyl, 2- or 3-chloropropyl, 2- or 4-chlorobutyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 2-hydroxysulfonylethyl, 3-hydroxysulfonylpropyl, 4-hydroxysulfonylbutyl, 2-carboxyethyl, 3-carboxypropyl or 4-carboxybutyl.
- Suitable diazo components of which the rest are, for example, 1,3-diaminobenzene, 2,4-diaminobenzenesulfonic acid, 2,5-diaminobenzenesulfonic acid, 2,4-diaminobenzoic acid, 2,4-diaminobenzene-1,5-disulfonic acid or 2,5-diaminobenzene-1,4- disulfonic acid.
- Residues of the coupling component of the formula are for example
- the rest are derived, for example, from aniline-2,4-disulfonic acid, N-methyl- or N-ethylaniline-2,4-disulfonic acid, aniline-2,5-disulfonic acid, N-methyl- or N-ethylaniline-2,5-disulfonic acid, 2-amino-4-hydroxysulfonylbenzoic acid, 2-amino-5-hydroxysulfonylbenzoic acid, 2-methylamino or 2-ethylamino-5-hydroxysulfonylbenzoic acid, 4-chloroaniline-2,5-disulfonic acid, 3-chloroaniline-4,6-disulfonic acid, 2 Chloraniline-4,5-disulfonic acid, 4-aminotoluene-2,5-disulfonic acid, 3-aminophthalic acid, 4-aminophthalic acid, aminoterephthalic acid, 1-aminonaphthalene-3,6- or -3,
- azo reactive dyes of the formula I in which the rest derived from the following diazo components: 2,4-diaminobenzenesulfonic acid, 2,5-diaminobenzenesulfonic acid or 2,4-diaminobenzene-1,5-disulfonic acid.
- azo reactive dyes of the formula I in which the ring A is not benzo-fused and n is 2.
- azo reactive dyes of the formula I in which the rest of the coupling components independently of one another have the formula
- azo reactive dyes of the formula I in which the sum of the hydroxysulfonyl radicals or the hydroxysulfonyl and carboxyl radicals together is 10.
- the azo reactive dyes of the formula I according to the invention can also occur as mixtures, in particular mixtures of those dyes which have 1-amino-8-hydroxynaphthalene-3,6- and -4,6-disulfonic acid as the coupling component.
- the mixtures can be produced by mechanical mixing or by mixing coupling. The mixing ratio can be selected as required.
- azo reactive dyes of the formula Ia correspond in the R2 is hydrogen or methyl and Z is hydrogen or hydroxysulfonyl and n, T, Hal, Y and the ring A each have the meaning given above.
- Azoreactive dyes which have the formula Ib correspond in the R2 is hydrogen or methyl and T has the meaning given above.
- the dyes according to the invention are preferably prepared by method a).
- the new reactive dyes of the formula I are advantageously suitable for dyeing or printing hydroxyl groups or nitrogen-containing organic substrates.
- Such substrates are, for example, leather or fiber material which predominantly contains natural or synthetic polyamides or natural or regenerated cellulose.
- the new dyes are preferably suitable for dyeing and printing textile material based on cotton.
- the violet dye of the formula was converted from 2- (2,5-dihydroxysulfonylphenylamino) -4-chloro-6- (4-amino-3-hydroxysulfonylphenylamino) -s-triazine and the coupling component from Example 1a) ( ⁇ max (water): 542.1 nm) obtained as the decalcium salt, which is comparable to the dye of Example 1 with regard to dyeing conditions, color strength and fastness properties.
- Example 37 NH-C2H4-OH ⁇ max : 512 nm
- 100 g of a cotton yarn were treated in a dyebath containing 1500 ml of water, 2.0 g of the dye from Example 2, 75 g of sodium sulfate and 30 g of soda. From 30 ° C, the temperature was raised to 60 ° C within 30 minutes and held at this value for 60 minutes.
- a cotton fabric was soaked on a three-roll pad at room temperature with a dyeing liquor which, in 1000 g of liquor, contained 16 g of the dye from Example 1, 100 g of sodium silicate (38 ° Bé), 50 g of sodium hydroxide solution (38 ° Bé) and 100 g of urea.
- the fabric After impregnation with a liquor pick-up of 70%, the fabric was rolled up and, after being covered with a film, stored in a moist state for 8 hours at room temperature.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4020769 | 1990-06-29 | ||
| DE4020769A DE4020769A1 (de) | 1990-06-29 | 1990-06-29 | Azoreaktivfarbstoffe mit mindestens zwei halogentriazinankern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0464448A1 true EP0464448A1 (fr) | 1992-01-08 |
| EP0464448B1 EP0464448B1 (fr) | 1994-08-31 |
Family
ID=6409355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP91109927A Expired - Lifetime EP0464448B1 (fr) | 1990-06-29 | 1991-06-18 | Colorants réactifs azoiques ayant au moins deux ancres halogénotriazine |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5223607A (fr) |
| EP (1) | EP0464448B1 (fr) |
| JP (1) | JPH04314761A (fr) |
| DE (2) | DE4020769A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0624629A1 (fr) * | 1993-05-14 | 1994-11-17 | Ciba-Geigy Ag | Colorants réactifs vis-à-vis des fibres, leur préparation et leur application |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4329420A1 (de) * | 1993-09-01 | 1995-03-02 | Bayer Ag | Azo-Reaktivfarbstoffe |
| US5886159A (en) * | 1996-08-23 | 1999-03-23 | Sumitomo Chemical Company, Limited | Bisazo compound and method for dyeing or printing fibrous materials using the same |
| CN115466524B (zh) * | 2022-09-02 | 2024-07-23 | 浙江劲光实业股份有限公司 | 一种活性染料的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1583387A (en) * | 1976-09-06 | 1981-01-28 | Nippon Kayaku Kk | Preparation of reactive bisazo dyestuffs based on h acid |
| EP0387589A2 (fr) * | 1989-03-13 | 1990-09-19 | BASF Aktiengesellschaft | Colorants réactifs ayant trois groupes réactifs |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5933718B2 (ja) * | 1975-09-29 | 1984-08-17 | 日本化薬株式会社 | セルロ−ス系繊維の染色法 |
| JPS6027696B2 (ja) * | 1976-08-27 | 1985-07-01 | 日本化薬株式会社 | トリアジン環を４個有するジスアゾ化合物及びその製造法 |
| JPS53111176A (en) * | 1978-03-06 | 1978-09-28 | Mitsubishi Chem Ind | Dyeing of cellulosic fiber |
| JPS6069163A (ja) * | 1983-09-26 | 1985-04-19 | Sumitomo Chem Co Ltd | ビスアゾ化合物およびそれを用いる染色または捺染法 |
-
1990
- 1990-06-29 DE DE4020769A patent/DE4020769A1/de not_active Withdrawn
-
1991
- 1991-06-18 DE DE59102715T patent/DE59102715D1/de not_active Expired - Lifetime
- 1991-06-18 EP EP91109927A patent/EP0464448B1/fr not_active Expired - Lifetime
- 1991-06-18 US US07/717,048 patent/US5223607A/en not_active Expired - Fee Related
- 1991-06-26 JP JP3154254A patent/JPH04314761A/ja not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1583387A (en) * | 1976-09-06 | 1981-01-28 | Nippon Kayaku Kk | Preparation of reactive bisazo dyestuffs based on h acid |
| EP0387589A2 (fr) * | 1989-03-13 | 1990-09-19 | BASF Aktiengesellschaft | Colorants réactifs ayant trois groupes réactifs |
Non-Patent Citations (1)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN, unexamined applications, C field, Band 9, Nr. 200, 16. August 1985 THE PATENT OFFICE JAPANESE GOVERNMENT Seite 124 C 298 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0624629A1 (fr) * | 1993-05-14 | 1994-11-17 | Ciba-Geigy Ag | Colorants réactifs vis-à-vis des fibres, leur préparation et leur application |
| US5484898A (en) * | 1993-05-14 | 1996-01-16 | Ciba-Geigy Corporation | Fibre-reactive disazo dyes which contain three triazine groups |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0464448B1 (fr) | 1994-08-31 |
| US5223607A (en) | 1993-06-29 |
| DE4020769A1 (de) | 1992-01-02 |
| JPH04314761A (ja) | 1992-11-05 |
| DE59102715D1 (de) | 1994-10-06 |
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